S$ 537 Find Cheap Flights from Chicago to Singapore – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 8-9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Sun, 6 Sep - Tue, 15 Sep
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
Air Canada Logo
06:15 - 20:12
SIN
-
ORD
26h 57m
2 stops
S$ 1,244Air Canada
Sat, 22 Aug - Wed, 9 Sep
Air Canada Logo
19:46 - 05:15
ORD
-
SIN
44h 29m
2 stops
Air Canada Logo
06:15 - 07:51
SIN
-
ORD
38h 36m
2 stops
S$ 1,246Air Canada
Mon, 7 Sep - Mon, 14 Sep
Multiple Airlines Logo
16:00 - 19:05
ORD
-
SIN
38h 05m
1 stop
Multiple Airlines Logo
06:15 - 20:12
SIN
-
ORD
26h 57m
2 stops
S$ 1,247Multiple Airlines
Sun, 6 Sep - Wed, 23 Sep
Delta Logo
16:39 - 19:15
MDW
-
SIN
37h 36m
2 stops
Delta Logo
07:30 - 22:44
SIN
-
MDW
28h 14m
2 stops
S$ 1,250Delta
Wed, 2 Sep - Wed, 30 Sep
Multiple Airlines Logo
21:10 - 09:40
ORD
-
SIN
23h 30m
1 stop
Multiple Airlines Logo
22:50 - 20:06
SIN
-
ORD
34h 16m
2 stops
S$ 1,250Multiple Airlines
Mon, 7 Sep - Wed, 16 Sep
Multiple Airlines Logo
16:00 - 19:05
ORD
-
SIN
38h 05m
1 stop
Multiple Airlines Logo
06:15 - 10:15
SIN
-
ORD
41h 00m
2 stops
S$ 1,251Multiple Airlines
Mon, 7 Sep - Mon, 14 Sep
Multiple Airlines Logo
16:00 - 05:30
ORD
-
SIN
24h 30m
1 stop
Multiple Airlines Logo
06:15 - 14:43
SIN
-
ORD
45h 28m
2 stops
S$ 1,253Multiple Airlines
Wed, 30 Sep - Mon, 5 Oct
Korean Air Logo
12:10 - 19:15
ORD
-
SIN
42h 05m
1 stop
Korean Air Logo
01:25 - 09:30
SIN
-
ORD
21h 05m
1 stop
S$ 1,255Korean Air
Mon, 14 Sep - Wed, 23 Sep
Air Canada Logo
19:48 - 05:15
ORD
-
SIN
44h 27m
1 stop
Air Canada Logo
08:10 - 14:43
SIN
-
ORD
43h 33m
2 stops
S$ 1,260Air Canada
Mon, 12 Oct - Tue, 27 Oct
Delta Logo
09:59 - 05:00
MDW
-
SIN
30h 01m
2 stops
Delta Logo
10:40 - 22:25
SIN
-
MDW
24h 45m
2 stops
S$ 1,269Delta
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is September, when tickets cost S$ 1,170 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of return tickets is S$ 2,558 and S$ 1,839 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low season

April

Cheapest flight

S$ 537
Best time to beat the crowds (23% less expensive on average)
Most popular time to fly (72% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
Etihad AirwaysOverall score based on 1486 reviews
7.3Comfort
7.8Crew
7.2Entertainment
7.6Boarding
7.2Food
Airline reviews

Connection booked by Etihad was delayed and upon arrival to counter they closed it and denied boarding although there was still 15 minutes to go . Manager Karen was very rude and did not want to listen seems there as overbooking and canceling boarding was the only solution..

2.0 MediocreAmr, Jul 2026
ORD - AUH
Read more Etihad Airways reviews

Connection booked by Etihad was delayed and upon arrival to counter they closed it and denied boarding although there was still 15 minutes to go . Manager Karen was very rude and did not want to listen seems there as overbooking and canceling boarding was the only solution..

They lost the baggage and said it was deleted from the system. I had baggage tag so was able to file the complaint but there was no PIR number and update so far

Good one but just notice that you have to ask several time to get water or coffee .

It was fantastic. The flight from Chicago to Abu Dahbi was fantastic. The crew, food and service were amazing. Everything was handled by the crew member assigned to us , Nicholas, was usually done before we asked for it. Highly recommend Etihad!

The food could be better. Toilets were smelly all along

Bad. Flight was very uncomfortable with narrow and shallow seats, very little food and water. I will not fly etihad again.

Good range of movies but lacking decent tv shows. Wifi was really expensive on this flight, considering flights under 7 hours have a $9.99 USD charge for streaming, to jump up to $24.99 for a 7 hour 40 flight seemed a little bit of a rip off. Staff are inattentive, and really need to improve on the customer experience. The new airport is fantastic, as is the new lounge, a huge upgrade from the old airport and lounge!

One thing is very important is you people not giving seat arrangement together to couple, senior citizen. You have to take care of senior citizen. Do not look about money. Money is not important everywhere. Make relationship strong is very very important. I like Etiyad air line out of all air line. Food was hot and delicious. Air hostess gave very good service, nice attitude, very good behaviour. I gave 10 out of 10 marks. Thanks Jivraj

Crew member took too long time to take back leftover food plates from passenger seats. Food was nice.Easy excellent checking.Guy at checking counter was really kind and helpful.Made our checking very quickly. Leftover food should be taken back ASAP. Because in economy class passanger have narrow space . In the long journey like this, passanger have difficulties to sit with the plates.overall experience was good.

crew as a whole is pretty mediocre. dont seem to care much for passengers. Asked 3 different crew for custom papers for immigration check in and they all said i could get it in the airport. have flown to india 3 times prior to this with Qatar and Emirates and they have always provided this paper ahead of landing to speed up the check in process. Also felt in general the crew is irritated and overworked. The one lady in my aisle from Chicago to Abu Dhabi was very pleasant but i was noticing the other crew were nice to each other but pretty cold with the passengers. Not what i usually have experienced from this type of overseas travel. Ive always felt the crew in qatar and emirates were overly sweet and pleasant but having seen the opposite this time i definitely prefer the former.

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.